4-(Trifluoromethyl)phenyl isocyanate → HCID 18980966, compound

HRID 482627Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]([N:16]([CH2:25][CH2:26][CH3:27])[C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[CH2:14][NH:13][N:12]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[F:28][C:29]([F:40])([F:39])[C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1>CCOCC>[F:28][C:29]([F:39])([F:40])[C:30]1[CH:31]=[CH:32][C:33]([NH:36][C:37]([N:13]2[CH2:14][CH:15]([N:16]([CH2:25][CH2:26][CH3:27])[C:17]([O:19][CH2:20][C:21]([Cl:22])([Cl:24])[Cl:23])=[O:18])[C:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[CH:6][CH:7]=3)=[N:12]2)=[O:38])=[CH:34][CH:35]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To an ether solution of 3-(4-propoxyphenyl)-4-(N-propyl-N-(2,2,2-trichloroethoxycarbonyl)amino)-4,5-dihydro-1H-pyrazole (Example 585e) (≤85 mmole) was added 12.7 g (68 mmole) of 4-trifluoromethylphenyl isocyanate. After stirring for 30 minutes, the mixture was concentrated in vacuo and dissolved in 200 ml of 50/50 diethyl ether/hexanes and cooled to -20° C. Crystals of the desired compound formed and were filtered yielding 23 g of the desired compound, mp 162°-163° C.

Workup

concentrationthe mixture was concentrated in vacuo
dissolutiondissolved in 200 ml of 50/50 diethyl ether/hexanes

Sources & evidence

ORD record: ord-25d1f06862ae4ebdb00001cad256d452
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05798311

Reaction notes

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